Cyclohexanol → HCID 86681313, compound

HRID 1778868Notes

Reaction equation

HRID 1778868 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C)C(=O)C.[H-].[Na+].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:18]=1[C:24]([F:27])([F:26])[F:25]>O>[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:18]=1[C:24]([F:27])([F:26])[F:25]

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 27733452-Bromo-6-fluorobenzotrifluoride

Product 1

HCID 86681313HCID 86681313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Cyclohexanol (214 mg) was added to N,N-dimethylacetamide (10 mL), and sodium hydride (60% in mineral oil, 86 mg) was added. The solution was mixed at room temperature for 15 minutes after which time 1-bromo-3-fluoro-2-(trifluoromethyl)benzene (400 mg) was added. The solution was then heated at 100° C. for 1 hour. The solution was cooled, added to water, and extracted with diethyl ether. The extract was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified on silica gel using 5% ethyl acetate in hexanes.

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureThe solution was cooled
  4. extractionextracted with diethyl ether
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. custompurified on silica gel using 5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d2ee2f176adb429999cc34bef8d6cab8
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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